heptopyranose

Base Information

• Chemical Name: heptopyranose
• CAS No.: 6946-18-5
• Molecular Formula: C7H14O7
• Molecular Weight: 210.184
• Mol file: 6946-18-5.mol

Synonyms:

Chemical Property of heptopyranose

Chemical Property:

• Vapor Pressure: 2.78E-12mmHg at 25°C
• Boiling Point: 504.3°Cat760mmHg
• Flash Point: 258.8°C
• Density: 1.81g/cm³

Purity/Quality:

90%,98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of heptopyranose

There total 20 articles about heptopyranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

benzyl 2,3-O-isopropylidene-β-L-glycero-D-manno-heptofuranoside (105592-29-8) → C10H18O7 + L-glycero-D-manno-heptose (6946-17-4,6946-18-5,13405-44-2,40825-95-4,84708-91-8,87172-44-9,87172-45-0,87172-48-3,87172-49-4,87172-52-9,87172-53-0,87172-56-3,87172-57-4,87172-60-9,87172-62-1,87172-63-2,87172-66-5,87172-67-6,87172-68-7,87173-39-5,87247-39-0,130272-67-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 20h; under 760.051 Torr;

DOI:10.1016/j.carres.2011.05.033

Reference yield:

(2S,3S,4S,5S,6S)-3,4,5,6-tetrabenzyloxytetrahydropyran-2-carbaldehyde (102046-36-6) → L-glycero-D-manno-heptose (6946-17-4,6946-18-5,13405-44-2,40825-95-4,84708-91-8,87172-44-9,87172-45-0,87172-48-3,87172-49-4,87172-52-9,87172-53-0,87172-56-3,87172-57-4,87172-60-9,87172-62-1,87172-63-2,87172-66-5,87172-67-6,87172-68-7,87173-39-5,87247-39-0,130272-67-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,2-dibromoethane / tetrahydrofuran / 2 h / 0 °C

2: 1.) NH₄Cl; 2.) H₂O₂ (30percent) / 1.) hydrolysis, 0 deg C; 2.) MeOH/THF, reflux, 15 h

3: H₂ / Pd/C

With hydrogen; dihydrogen peroxide; ammonium chloride; ethylene dibromide; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1002/recl.19881070706

Reference yield:

benzyl 6-O-triphenylmethyl-α-D-mannopyranoside (77455-30-2) → L-glycero-D-manno-heptose (6946-17-4,6946-18-5,13405-44-2,40825-95-4,84708-91-8,87172-44-9,87172-45-0,87172-48-3,87172-49-4,87172-52-9,87172-53-0,87172-56-3,87172-57-4,87172-60-9,87172-62-1,87172-63-2,87172-66-5,87172-67-6,87172-68-7,87173-39-5,87247-39-0,130272-67-2)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydroxide / dimethylsulfoxide / 1.5 h / Ambient temperature

2: trifluoroacetic acid / dioxane; methanol / Heating

3: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -60 °C

4: 34 percent / pyridine / 0 deg C, 2 h, RT, 24 h

5: lithium aluminum hydride / various solvent(s) / 0.17 h / 0 °C

6: 35.6 percent / sodium nitrite, 0.2M acetic acid / dioxane; H₂O / 0 deg C, RT, 5 h

7: H₂ / 10percent Pd/C

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; acetic acid; dimethyl sulfoxide; trifluoroacetic acid; sodium nitrite; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/0008-6215(86)80013-1

upstream raw materials:

1,2,3,4,6,7-Hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose

7-O-Pivaloyl-D-glycero-D-galacto-heptose-trimethylendithioacetal

2,3,4,5,6-Penta-O-acetyl-7-O-pivaloyl-D-glycero-D-galacto-heptose-trimethylendithioacetal

benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside

Downstream raw materials:

methyl L-glycero-α-D-manno-heptopyranoside

methyl L-glycero-α-D-manno-heptopyranoside

1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose

1-(N,N-dibenzyl)amino-1-deoxy-α-D-gluco-hept-2-ulopyranose

Refernces

• 1、 Grzeszczyk, Barbara,Holst, Otto,Mueller-Loennies, Sven,Zamojski, Aleksander. "Five monophosphates of methyl L-glycero-α-D-manno-heptopyranoside: Synthesis, hydrolysis and migrations". . p. 55 - 67. Retrieved 2007/10/03.
• 2、 Paulsen, Hans,Schueller, Matthias,Heitmann, Axel,Nashed, Mina A.,Redlich, Hartmut. "Branched and Chain-extended Sugars, XXX.- Diastereoselective Synthesis of L-glycero-D-manno-Heptose, a Constituent of the Inner Core Region of Lipopolysaccharides". . p. 675 - 686. Retrieved 2007/10/02.